Structure Database (LMSD)

Common Name
Anandamide-d4 (20:4, n-6)
Systematic Name
N-(2-hydroxyethyl-1,1,2,2-d4)-5Z,8Z,11Z,14Z-eicosatetraenamide
Synonyms
  • Anandamide
  • Anandamide(20:4, n-6)
  • N-arachidonoyl ethanolamine
  • arachidonoylethanolamide
  • Arachidonoyl-EA
  • Arachidonoyl ethanolamide
  • AEA
LM ID
LMFA08040056
Formula
C22H33D4NO2
Exact Mass
Calculate m/z
351.307537
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl ethanolamines (endocannabinoids) [FA0804]

Biological Context

Arachidonoyl ethanolamide-d4 (AEA-d4) is intended for use as an internal standard for the quantification of AEA by GC- or LC-mass spectrometry. AEA is the ethanolamine amide of arachidonic acid, first isolated from porcine brain.1 It is an endogenous cannabinoid neurotransmitter that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors and mimics the pharmacologic effects of Δ9-THC.2 AEA inhibits the specific binding of [3H]-HU-243 to synaptosomal membranes with a Ki value of 52 nM, compared to 46 nM for Δ9-THC.1

This information has been provided by Cayman Chemical

References

1. Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA 90(16), 7656-7660 (1993).
2. Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090), 1946-1949 (1992).

References

Comments
Synthetic deuterated standard

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
LGEQQWMQCRIYKG-KALLKTRHSA-N
InChi (Click to copy)
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-/i20D2,21D2
SMILES (Click to copy)
C(=C/C/C=C\CCCC(=O)NC([2H])([2H])C([2H])([2H])O)/C/C=C\C/C=C\CCCCC

Other Databases

PubChem CID
24762159
Cayman ID
10011178

Admin

Created at
-
Updated at
29th Jan 2021